Cyclohexene, 3-(1,5-dimethyl-4-hexenyl)-6-methylene-, [S-(R*,S*)]-
- Formula: C15H24
- Molecular weight: 204.3511
- IUPAC Standard InChI: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14-15H,3,5,7,9,11H2,1-2,4H3/t14?,15-/m1/s1
- IUPAC Standard InChIKey: PHWISBHSBNDZDX-YSSOQSIOSA-N
- CAS Registry Number: 20307-83-9
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Stereoisomers:
- Other names: β-Sesquiphellandrene; 3-((1S)-1,5-Dimethyl-4-hexenyl)-6-methylene-1-cyclohexene, (3R)-; (-)-β-Sesquiphellandrene; (R)-3-Methylene-6-((S)-6-methylhept-5-en-2-yl)cyclohex-1-ene; Sesquiphellandrene; β-Sesquiphellanderene
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
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Van Den Dool and Kratz RI, polar column, temperature ramp
Go To: Top, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | RTX-Wax | RTX-Wax | BP-20 | HP-Wax | BP-20 |
| Column length (m) | 60. | 60. | 50. | 30. | 50. |
| Carrier gas | He | He | He | N2 | He |
| Substrate | |||||
| Column diameter (mm) | 0.22 | 0.22 | 0.22 | 0.25 | 0.22 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 60. | 60. | 60. | 60. |
| Tend (C) | 230. | 230. | 220. | 220. | 220. |
| Heat rate (K/min) | 2. | 2. | 2. | 5. | 2. |
| Initial hold (min) | 10. | ||||
| Final hold (min) | 30. | 35. | 20. | 20. | |
| I | 1765. | 1761. | 1766. | 1783. | 1768. |
| Reference | Bendahou, Muselli, et al., 2008 | Paolini J., Costa J., et al., 2007 | Duquesnoy, Dinh, et al., 2006 | Flamini, Tebano, et al., 2006 | Gonny, Cavaleiro, et al., 2006 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Supelcowax-10 | BP-20 | DB-Wax | PEG | HP-Wax |
| Column length (m) | 30. | 50. | 60. | 30. | 30. |
| Carrier gas | He | He | N2 | N2 | He |
| Substrate | |||||
| Column diameter (mm) | 0.2 | 0.22 | 0.25 | 0.32 | 0.25 |
| Phase thickness (μm) | 0.2 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 70. | 60. | 70. | 50. | 60. |
| Tend (C) | 220. | 220. | 230. | 220. | 240. |
| Heat rate (K/min) | 3. | 2. | 2. | 2. | 3. |
| Initial hold (min) | 2. | 3. | |||
| Final hold (min) | 15. | 20. | 20. | 15. | |
| I | 1763. | 1767. | 1780. | 1776. | 1773. |
| Reference | Pinto, Pina-Vaz, et al., 2006 | Boti J.B., Koukoua G., et al., 2005 | Choi, 2005 | Dob, Berramdane, et al., 2005 | Flamini, Bader, et al., 2004 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | BP-20 | DB-Wax | RTX-Wax | DB-Wax | DB-Wax |
| Column length (m) | 50. | 30. | 60. | 60. | 60. |
| Carrier gas | He | He | N2 | N2 | |
| Substrate | |||||
| Column diameter (mm) | 0.22 | 0.25 | 0.22 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 40. | 60. | 70. | 70. |
| Tend (C) | 220. | 200. | 230. | 230. | 230. |
| Heat rate (K/min) | 2. | 4. | 2. | 2. | 2. |
| Initial hold (min) | 5. | 2. | |||
| Final hold (min) | 20. | 20. | 45. | 20. | 20. |
| I | 1768. | 1767. | 1758. | 1780. | 1772. |
| Reference | Gonny, Bradesi, et al., 2004 | Zheng, Kim, et al., 2004 | Cavalli, Tomi, et al., 2003 | Choi, 2003 | Choi, Kim. M.-S.L., et al., 2002 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-Wax | DB-Wax | BP-20 | Carbowax 20M | DB-Wax |
| Column length (m) | 60. | 60. | 50. | 25. | 60. |
| Carrier gas | He | N2 | He | H2 | |
| Substrate | |||||
| Column diameter (mm) | 0.5 | 0.25 | 0.22 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.32 | 0.25 | 0.25 | 0.3 | 0.25 |
| Tstart (C) | 40. | 70. | 60. | 50. | 40. |
| Tend (C) | 290. | 230. | 220. | 200. | 200. |
| Heat rate (K/min) | 4. | 2. | 2. | 3. | 3. |
| Initial hold (min) | 2. | 2. | 1. | 5. | |
| Final hold (min) | 5. | 20. | 20. | 20. | 60. |
| I | 1778. | 1777. | 1762. | 1768. | 1771. |
| Reference | Bartley and Jacobs, 2000 | Choi and Sawamura, 2000 | Mazzoni, Tomi, et al., 1999 | Bicchi, Rubiolo, et al., 1998 | Cha, Kim, et al., 1998 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-Wax | CP-Wax 52CB | HP-20M | Carbowax 20M | Carbowax 20M |
| Column length (m) | 25. | 50. | 50. | 60. | 60. |
| Carrier gas | He | H2 | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.32 | 0.25 | 0.32 | 0.32 |
| Phase thickness (μm) | 0.25 | ||||
| Tstart (C) | 50. | 50. | 60. | 50. | 50. |
| Tend (C) | 240. | 200. | 190. | 225. | 225. |
| Heat rate (K/min) | 4. | 1.5 | 3. | 1.5 | 1.5 |
| Initial hold (min) | 3. | 10. | |||
| Final hold (min) | 40. | 80. | 80. | ||
| I | 1766. | 1789. | 1782. | 1748. | 1743. |
| Reference | Möllenbeck, König, et al., 1997 | Wu and Yang, 1994 | Chung, Eiserich, et al., 1993 | Chen and Ho, 1988 | Chen and Ho, 1988 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary |
|---|---|
| Active phase | Carbowax 20M |
| Column length (m) | 60. |
| Carrier gas | He |
| Substrate | |
| Column diameter (mm) | 0.32 |
| Phase thickness (μm) | |
| Tstart (C) | 50. |
| Tend (C) | 225. |
| Heat rate (K/min) | 1.5 |
| Initial hold (min) | |
| Final hold (min) | 80. |
| I | 1743. |
| Reference | Chen and Ho, 1988 |
| Comment | MSDC-RI |
References
Go To: Top, Van Den Dool and Kratz RI, polar column, temperature ramp, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bendahou, Muselli, et al., 2008
Bendahou, M.; Muselli, A.; Grignon-Dubois, M.; Benyoucef, M.; Desjobert, J.-M.; Bernardini, A.-F.; Costa, J.,
Antimicrobial activity and chemical composition of Origanum glandulosum Desf. essential oil and extract obtained by microwave extraction: Comparison with hydrodistillation,
Food Chem., 2008, 106, 1, 132-139, https://doi.org/10.1016/j.foodchem.2007.05.050
. [all data]
Paolini J., Costa J., et al., 2007
Paolini J.; Costa J.; Bernardini A.F.,
Analysis of the essential oil from the roots of Eupatorium cannabinum subsp corsicum (L.) by GC, GC-MS and C-13-NMR,
Phytochem. Anal., 2007, 18, 3, 235-244, https://doi.org/10.1002/pca.977
. [all data]
Duquesnoy, Dinh, et al., 2006
Duquesnoy, E.; Dinh, N.H.; Castola, V.; Casanova, J.,
Composition of a Pyrolytic oil from Cupressus funebris Endl. of Vietnamese origin,
Flavour Fragr. J., 2006, 21, 3, 453-457, https://doi.org/10.1002/ffj.1676
. [all data]
Flamini, Tebano, et al., 2006
Flamini, G.; Tebano, M.; Cioni, P.L.; Bagci, Y.; Dural, H.; Ertugrul, K.; Uysal, T.; Savran, A.,
A multivariate statistical approach to Centaurea classification using essential oil composition data of some species from Turkey,
Pl. Syst. Evol., 2006, 261, 1-4, 217-228, https://doi.org/10.1007/s00606-006-0448-3
. [all data]
Gonny, Cavaleiro, et al., 2006
Gonny, M.; Cavaleiro, C.; Salgueiro, L.; Casanova, J.,
Analysis of Juniperus communis subsp. alpina needle, berry, wood and root oils by combination of GC, GC/MS and 13C-NMR,
Flavour Fragr. J., 2006, 21, 1, 99-106, https://doi.org/10.1002/ffj.1527
. [all data]
Pinto, Pina-Vaz, et al., 2006
Pinto, E.; Pina-Vaz, C.; Salgueiro, L.; Goncalves, M.J.; Costa-de-Oliveira, S.; Cavaleiro, C.; Palmeira, A.; Rodrigues, A.; Martinez-de-Oliveira, J.,
Antifuncal activity of the essential oil Thymus pulegioides on Candida, Aspergillus and dermatophyte species,
Journal of Medical Microbiology, 2006, 55, 10, 1367-1373, https://doi.org/10.1099/jmm.0.46443-0
. [all data]
Boti J.B., Koukoua G., et al., 2005
Boti J.B.; Koukoua G.; N'Guessan T.Y.; Muselli A.; Bernardini A.F.; Casanova J.,
Composition of the leaf, stem bark and root bark oils of Isolona cooperi investigated by GC (retention index), GC-MS and C-13-NMR spectroscopy,
Phytochem. Anal., 2005, 16, 5, 357-363, https://doi.org/10.1002/pca.857
. [all data]
Choi, 2005
Choi, H.-S.,
Characteristic odor components of kumquat (Fortunella japonica Swingle) peel oil,
J. Agric. Food Chem., 2005, 53, 5, 1642-1647, https://doi.org/10.1021/jf040324x
. [all data]
Dob, Berramdane, et al., 2005
Dob, T.; Berramdane, T.; Chelgoum, C.,
Chemical composition of essential oil of Pinus halepensis Miller growing in Algeria,
C.R. Chim., 2005, 8, 11-12, 1939-1945, https://doi.org/10.1016/j.crci.2005.05.007
. [all data]
Flamini, Bader, et al., 2004
Flamini, G.; Bader, A.; Cioni, P.L.; Katbeh-Bader, A.; Morelli, I.,
Composition of the essential oil of leaves, galls, and ripe and unripe fruits of Jordian Pistacia palaestina Boiss.,
J. Agric. Food Chem., 2004, 52, 3, 572-576, https://doi.org/10.1021/jf034773t
. [all data]
Gonny, Bradesi, et al., 2004
Gonny, M.; Bradesi, P.; Casanova, J.,
Identification of the components of the essential oil from wild Corsican Daucus carota L. using 13C-NMR spectroscopy,
Flavour Fragr. J., 2004, 19, 5, 424-433, https://doi.org/10.1002/ffj.1330
. [all data]
Zheng, Kim, et al., 2004
Zheng, C.H.; Kim, T.H.; Kim, K.H.; Leem, Y.H.; Lee, H.J.,
Characterization of potent aroma compounds in Chrysanthemum coronarium L. (Garland) using aroma extract dilution analysis,
Flavour Fragr. J., 2004, 19, 5, 401-405, https://doi.org/10.1002/ffj.1447
. [all data]
Cavalli, Tomi, et al., 2003
Cavalli, J.-F.; Tomi, F.; Bernardini, A.-F.; Casanova, J.,
Composition and chemical variability of the bark oil of Cedrelopsis grevei H. Baillon from Madagascar,
Flavour Fragr. J., 2003, 18, 6, 532-538, https://doi.org/10.1002/ffj.1263
. [all data]
Choi, 2003
Choi, H.-S.,
Character impact odorants of Citrus Hallabong [(C. unshiu Marcov × C. sinensis Osbeck) × C. reticulata Blanco] cold-pressed peel oil,
J. Agric. Food Chem., 2003, 51, 9, 2687-2692, https://doi.org/10.1021/jf021069o
. [all data]
Choi, Kim. M.-S.L., et al., 2002
Choi, H.-S.; Kim. M.-S.L.; Sawamura, M.,
Constituents of the essential oil of cnidium officinale Makino, a Korean medicinal plant,
Flavour Fragr. J., 2002, 17, 1, 49-53, https://doi.org/10.1002/ffj.1038
. [all data]
Bartley and Jacobs, 2000
Bartley, J.P.; Jacobs, A.L.,
Effects of drying on flavour compounds in Australian-grown ginger (Zingiber officinale),
J. Sci. Food Agric., 2000, 80, 2, 209-215, https://doi.org/10.1002/(SICI)1097-0010(20000115)80:2<209::AID-JSFA516>3.0.CO;2-8
. [all data]
Choi and Sawamura, 2000
Choi, H.-S.; Sawamura, M.,
Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu),
J. Agric. Food Chem., 2000, 48, 10, 4868-4873, https://doi.org/10.1021/jf000651e
. [all data]
Mazzoni, Tomi, et al., 1999
Mazzoni, V.; Tomi, F.; Casanova, J.,
A daucane-type sesquiterpene from Faucus carota seed oil,
Flavour Fragr. J., 1999, 14, 5, 268-272, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<268::AID-FFJ823>3.0.CO;2-Z
. [all data]
Bicchi, Rubiolo, et al., 1998
Bicchi, C.; Rubiolo, P.; Marschall, H.; Weyerstahl, P.; Laurent, R.,
Constituents of Artemisia roxburghiana Besser essential oil,
Flavour Fragr. J., 1998, 13, 1, 40-46, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<40::AID-FFJ688>3.0.CO;2-Z
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Cha, Kim, et al., 1998
Cha, Y.J.; Kim, H.; Cadwallader, K.R.,
Aroma-active compounds in Kimchi during fermentation,
J. Agric. Food Chem., 1998, 46, 5, 1944-1953, https://doi.org/10.1021/jf9706991
. [all data]
Möllenbeck, König, et al., 1997
Möllenbeck, S.; König, T.; Schreier, P.; Schwab, W.; Rajaonarivony, J.; Ranarivelo, L.,
Chemical composition and analyses of enantiomers of essential oils from Madagascar,
Flavour Fragr. J., 1997, 12, 2, 63-69, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z
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Wu and Yang, 1994
Wu, J.-J.; Yang, J.-S.,
Effects of γ irradiation on the volatile compounds of ginger rhizome (Zingiber officinale Roscoe),
J. Agric. Food Chem., 1994, 42, 11, 2574-2577, https://doi.org/10.1021/jf00047a038
. [all data]
Chung, Eiserich, et al., 1993
Chung, T.Y.; Eiserich, J.P.; Shibamoto, T.,
Volatile compounds isolated from edible Korean chamchwi (Aster scaber Thunb),
J. Agric. Food Chem., 1993, 41, 10, 1693-1697, https://doi.org/10.1021/jf00034a033
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Chen and Ho, 1988
Chen, C.-C.; Ho, C.-T.,
Gas chromatographic analysis of volatile components of ginger oil (Zingiber officinale Roscoe) extracted with liquid carbon dioxide,
J. Agric. Food Chem., 1988, 36, 2, 322-328, https://doi.org/10.1021/jf00080a020
. [all data]
Notes
Go To: Top, Van Den Dool and Kratz RI, polar column, temperature ramp, References
- Symbols used in this document:
Tend Final temperature Tstart Initial temperature - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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